The Highland School District became a reality in 1962 following a favorable consolidation vote in Ash Flat and Hardy. Before the votes were actually counted; however, many people doubted the consolidation would pass. The Ash Flat School District and the Hardy School District were rivals to some degree; however, the parents were more upset about losing their hometown schools. They were somewhat mollified by the fact that younger children would stay "home". The Ash Flat and Hardy school buildings were to be used for only grades 1-6 after a new high school was built. The location of the school was only logical, halfway between the two towns. The doors to the new high school first opened in August 1964 with the first senior class graduating in May 1965. Some six years later a growth in numbers forced the building of a new grade school, Cherokee Elementary, and even grade school children were then bused to the new school. Only seven years later, a further increase in numbers of students caused the district to build a third building, Highland Middle School. Highland High School received North Central Association (NCA) accreditation in 1975, with Highland Middle School and Cherokee Elementary School receiving NCA accreditation in 1999.
The Highland School District covers an area of 261 square miles, making it the 45th largest school district in Arkansas. The school campuses are centrally located on eighty acres in Highland. Today, Cherokee Elementary School houses K-4, but it also has a Head Start program on campus for four-year-olds. Highland Middle School has grades 5-7, and Highland High School includes grades 8-12. All three buildings have been expanded with new wings since their initial construction. In addition, the high school campus has added four new buildings: a Chapter One/Title I Math and Reading Lab, a vocational building, a band building, and a new building just for eighth graders. The district operates on a $7 million dollar annual budget. The school colors are red and gray, and the school mascot is the Rebel. There has been some discussion about the possible need of changing the mascot as some schools have been forced to do, but there is a great deal of impassioned resistance to the change.
Highland School District has enjoyed a great deal of community support and is respected by most people. There is a loyalty to the system among teachers and administrators, and there has never been a strike by the teachers. Another indication of the good relations present among the administration, the teachers, and the community is that Mr. A.L. Hutson had been superintendent of the Hardy School District before becoming Highland’s first superintendent. When Hutson retired in 1986, Mr. Jack Kimbrell, who had been the high school principal since 1979, took over as the new superintendent. Mr. Kimbrell went on to become highly regarded throughout the state as a school administrator. He served as President of the Arkansas Association of School Administrators and received the Superintendent of the Year award in 1999. Kimbrell retired the end of the 1999-2000 school year. Mr. Ronnie Brogdon began his duties on July 1, 2000. He faithfully served the Highland School District until June 30, 2010. During his ten years of service, Mr. Brogdon served as President of the Arkansas Association of School Administrators during the 2007-08 school year and was a member of the Arkansas Rural Education Association. He was also recognized as the Northeast Arkansas Superintendent of the Year in 2003.
Beginning July 1, 2010, Mr. James Floyd was chosen by the school board to lead the Highland District.